Bucket List: Milking

Sarah fucks Mark's arse with various toys to cross an entry off her sexual bucket list

Sex Bucket List Rules.

A list of sexual fantasies to complete before we kick the bucket!

We each have our own list. We take turns to choose from our lists Fantasies can be as simple or as complicated as you like. If a fantasy needs props then it’s the owner of the fantasies job to provide them. If you have a fantasy you’re not allowed to introduce it in bed before bucket night! If you’re not comfortable with the fantasy you can say No. No involvement of other people without mutual agreement. Safe word is "Access Denied!"

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Two whole weeks went by since we’d last had the chance to cross off more of our bucket list. We’d had sex plenty of times but we’d come to an unspoken agreement that bucket list nights would be special. I’d started paying more attention to Sarah’s nipples during foreplay and fucking since her revelation that she enjoyed having them twisted, bitten and sucked as hard as I could. I’d also fucked her arse twice more since the bucket list night, once gently in the spoons position and the second time with her riding my cock as she’d done the first time. She’d also started dressing for sex more, stockings and heels left on, more kinky underwear appearing in the post.

One package arrived on Saturday morning as we sat having breakfast in the morning sun on the balcony. Sarah opened it, caught site of the contents and immediately shut the lid. When I pressed her to reveal the contents she smiled and said they were for the bucket sex session we were having tomorrow afternoon. My grin widened until I remembered her words from our last session – “we shall see where your limits lie!”

Sunday morning was spent with breakfast followed by a walk in the park with Sarah’s sister and nephew. I have to admit to some distraction wondering what was in store for me when we got back to Sarah’s flat. Eventually we said our goodbyes and headed back to the car for the short drive home.

Finally we made it back to the flat. Sarah unlocked the front door and walked in.

‘I want you to go and have another shower. Make sure your bum is clean please.’ Sarah said with a smile.

‘Dare I ask?’ I said with a mixture of trepidation and excitement.

‘It’s my turn to be dominant. I want you knelt down in front of the sofa. I’m going to kneel behind you, rim you, stick my fingers in your bum to lube you up then fuck you with a selection of different sized butt plugs and, if you’re up for it, a vibrator. All the time I’m going to be milking your cock until you cum.’ Sarah explained.

‘Can I see the toys before you shove them where the sun don’t shine?’ I asked, half jokingly.

‘Of course you can. Go have a shower while I get ready. Don’t come out of the bathroom until I give you permission.’

I had a hot shower and made sure everything was nice and clean for Sarah then slowly dried myself thinking about what was about to happen. I’d never had anything up my bum, not even the doctors finger. I’ve always assumed my bum was ‘exit only’ but as I’ve happily fucked Sarah’s arse three times now, not to mention fingering and licking it, I couldn’t really turn around and tell her that! I realised I was getting hard thinking about it!

‘You can come out now and assume the position.’ Sarah shouted from outside the bathroom.

I walked naked into the living room to find Sarah had been busy. Her expensive rug had been rolled up and put to one side and a towel covered cushion put down over the laminate floor for me to kneel on. Sarah’s full length mirror had been wheeled from her bedroom and was standing at the end of the sofa so I could look down and see what she was doing to me. On the coffee table stood three vibrant, pink butt plugs starting with a small thin one, a medium sized one that didn’t seem much bigger than the small one and finally the large one that looked about double the circumference of the smallest plug! I suddenly realised I should be more anxious about width than length! I knelt on the towel and leaned forward on to the leather sofa.

‘What do you think?’ Sarah asked from the doorway to the kitchen.

My cock came to attention as I checked Sarah out. She was wearing a pair of black tights with knee length, shiny black high heeled boots that clung to the contours of her calves. On top she was wearing a second pair of tights with the crutch cut out and pulled over her head like a long sleeved t-shirt. The feet had been left in and covered her hands. Her big tits were pressed against her body by the tight, transparent fabric and her hard nipples were straining about the nylon trying to get out.

‘Wow!’ I said as she walked towards me. For the first time I noticed she had a dildo tucked into the waist band of her tights. It was the same colour as the butt plugs but was longer and had a control on the bottom of it for vibration I guessed.

‘You can look at us in the mirror but you can’t move.’ Sarah purred kneeling on a cushion behind me.

My cock was rock hard and pressed against the leather sofa. Sarah pulled it back between my legs and stroked it with her nylon covered hand. Her other hand stroked my lower back, bum and the backs of my thighs. I felt her breath on my arse as she leant forward to examine my bum.

I moaned in response and felt her hand squeeze my cock. I loved the feeling of the cool nylon on my hot cock and wondered if I’d be able to control myself for any decent amount of time. Sarah’s face moved closer to my bum and I almost shot my load as her long tongue suddenly licked my arsehole.

‘Oh Christ!’ I muttered as Sarah’s tongue started to explore my puckered hole.

Her hand left my cock and I felt a hand on each buttock spreading me for her inspection. I suddenly remembered the mirror and turned my head to get a good look. Sarah was on her knees behind me, leaning forward to tease my arse. Her heavy boobs were hanging beneath her, stretching the nylon tight. I saw her head move closer to me and felt her tongue pressing harder against my arsehole. No teasing now, Sarah was rimming me as I’d been rimming her for the last couple of weeks; her tongue was pressing hard against my anus and pushing past the tight muscle to explore inside. It felt fantastic!

Sarah rimmed me for a couple of minutes, her hands stayed on my cheeks to keep me spread for her. I watched her every move in the mirror fighting the urge to reach behind me and grab my cock to bring myself off. Finally she stopped and leaned back, her hands slapped a cheek each making me yelp in surprise.

‘I promised you fingers but it looks like we’re going to have to move directly on to the butt plugs.’ Sarah laughed holding up her nylon covered hands.

‘Maybe next time!’ I quipped.

Sarah picked up the smallest of the butt plugs, sucked it then pressed the end against my arsehole. With a quick push half of the 4” length disappeared into my spit lubricated butt. Sarah stroked my bum with one hand and pushed the butt plug all the way in. I breathed deeply but there was no pain, just pressure in my bum. It felt good, especially if I clenched my bum around it.

‘Comfortable?’’ she asked smiling at me in the mirror.

‘Feels really good’ I said with a sigh.

‘You should see how it looks. Oh wait, you can!’ She said standing up and walking to a set of drawers by the television.

‘Smile!’ Sarah said and I saw a flash go off as she took a picture of me with her camera.

She pressed a few buttons then handed me the camera so I could see the pink butt plug sticking out of my arse. I handed back the camera and Sarah took a few more shots of my bum and my cock with her hand stroking me.

‘You know this middle sized plug isn’t that much bigger than the one you have in you. I think I’ll have this one’ Sarah said putting the camera down and reaching for the middle sized butt plug.

I watched in the mirror as took the long dildo from her waist band and put it on the coffee table. She pulled her tights down, turning her back to the mirror so I got a good view of what she was about to do. I heard rather than saw her lube up the plug then watched as she reached behind and pushed the butt plug up her own bum. It took her a couple of attempts to get the angle right but eventually she got it right inside her and pulled her tights back up.

‘I see what you mean about it feeling good baby,’ she grinned kneeling behind me once more.

I started to answer but Sarah had grabbed hold of my butt plug, pulled it out and pushed it back into me with a twisting motion that made me use all my breath to moan. I felt coldness as lube was squeezed on to my arse and spread around and in my bum with the small dildo.

‘Deeper or wider? That is the question now.’ Sarah said half to herself.

I felt the small dildo removed from my arse and saw Sarah pick up the larger butt plug. She held it up with the small one and I could see it was about an inch and a half longer but the thinnest part of the taper was wider than the thickest part of the plug I’d just had up my arse. Sarah also picked up the long dildo and appeared to consider that for a minute before putting it back on the table and kneeling behind me once more.

I felt the rubber cock press against then stretch my arse open. Sarah gently but firmly pushed the plug up my well lubricated arsehole. I felt the girth but wasn’t in any pain. In fact I was enjoying being penetrated and pushed my arse back to encourage Sarah to get the whole thing in me.

‘You slut!’ she laughed, slapping my arse and pushing the butt plug all the way in with one hard push.

‘Oh fuck!’ I yelped in surprise as the widest part of the dildo penetrated me.

‘Oh you slut, it’s in you!’ Sarah squealed in delight and began taking more pictures.

‘Get up and walk to the kitchen and back slut boy.’

I stood up and shuffled to across the living room floor, not sure if the butt plug would stay put. I realised it wasn’t going anywhere by the time I walked the 15’ to the kitchen and strode back again. My cock had softened as Sarah had been inserting the butt plug but it was hard again by the time I got back to the sofa and knelt down again. Sarah pushed her hand against the dildo pushing it deeper.

‘You know I think I want this in my bum.’ She said, twisting it around inside me, ‘then I think I want to fuck you with the vibe.’

My cock twitched with excitement and I felt Sarah pull the butt plug out, stretching my arsehole wide as it came out with a wet plop. Once again Sarah pulled her tights down her thighs and reached behind her. The medium sized dildo came out with a plop and was discarded on the floor. Sarah turned around so her back was to me and rested the large plug on my bum.

‘Hold it for me Mark.’

I put my right hand on my bum and she handed me the dildo. I held it base down against my arse and watched Sarah pour lube over it then spread it around. I started to wonder what freshly lubed nylon would feel like on my cock but was distracted as Sarah sat on the dildo. It took her a couple of attempts to get all the butt plug into her arse and when it was fully seated she squirmed her bum against mine briefly then stood up and pulled her tights back up.

‘God that’s nice and big isn’t it!’ Sarah exclaimed as she walked around the room before returning to her cushion and kneeling behind me.

Sarah reached for the vibrator and pushed the end against my arsehole, three inches of the nine inch toy sliding into my wet, slipper bum. Sarah grabbed my cock with her right hand and I got to find out what lubricated nylon felt like – fucking fantastic! I started to push my arse back to get more of the long vibe in my arse. Sarah squeezed my hard cock and pushed another couple of inches in.

‘Oh you little slut, you want all this don’t you?’

‘Yes please mistress.’ I said softly.

Sarah pushed the dildo deep into my arse then turned the end switch to make it vibrate. She started to fuck me hard with the vibrating rubber cock as she milked me with her left hand. I spread my arms out on the sofa and pushed my arse back against the dildo as she thrust it into me. My guts and groin were on fire and I was soon gasping that I was about to cum. Sarah pushed the dildo deep inside my arse and tightened her grip on my prick. I felt her free hand move under me so the head of my cock was rubbing against the wet nylon as she milked me with her left hand. That was it; I lost it completely and began to cum into Sarah’s hand as my arse pushed the vibrating dildo out of my arse. Sarah leaned forward and used her shoulder to push the dildo back into my bum making me squirt cum again.

When I was empty Sarah pulled the dildo out of my arse and dropped it on the floor where it continued to vibrate. Sarah pulled me up and offered me her cum soaked hand to lick clean. I gently held her wrist and licked the puddle of cum dry then kissed her, our tongues twirling around each others. Eventually we broke apart, switched off the vibrator and pulled the butt plug out of Sarah’s bum giving her a mild orgasm as it popped out of her bum. We stripped and showered together before settling down on the sofa to have a look at the pictures Sarah had taken. I was shocked at the amount of gape my arse had when the large plug had been pulled out!

‘Like or no like?’ Sarah asked.

‘Like. Very much in fact. I loved you having a plug in too. I think I may have an addition to my list based on that!’ I smiled.

‘I don’t think I’m a very good dominatrix,’ Sarah said with a sigh, ‘all the time I was dominating you I just wanted to turn you over and ride your cock while you squeezed my nipples!’

‘Next time we’ll switch when you want to!’ I laughed kissing her neck.

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